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The constituents from the needles of the pine tree, Pinus densiflora, were purified and investigated for antithrombotic activity. The needles were initially extracted three times with 70% ethanol, and the extract was sequentially fractionated with chloroform and n-butanol. The aqueous layer formed after n-butanol fractionation was subjected to purification by medium pressure and high pressure liquid chromatography. The two neolignans, 2, 3-dihydro?7?hydroxyl?3?hydroxymethyl?2-(4´-hydroxyl ?3-methoxyphenyl)?5?benzofuranpropanol?3?O?α-rhamnopyranoside (a neolignan glycoside) and 2, 3-dihyro-3-hydroxymethyl-7-methoxy-2-(4´-hydroxyphenyl-3´-methoxy)-5-benxofuran propanol 4´-O-α-rhamnopyranoside (icariside E4) were identified by 1H and 13C NMR spectra. The effect of the purified compounds, the neolignan glycoside and icariside E4 on thrombin inhibition were investigated by measuring thrombin clotting time in plasma. As a result, the clotting of the neolignan glycoside was delayed four times compared to that of icariside E4. In addition, an analysis of the inhibition effect by changing the concentration showed that the clotting time was delayed in accordance with an increase in the concentration of the neolignan glycoside. Furthermore, we examined the interaction of thrombin and fibrinogen to clarify the action mechanism. As a result, the delay of clotting time in the response of thrombin and pure fibrinogen may indicate that neolignan glycosides inhibit the thrombin action in a direct manner, leading to the suppression of fibrin generation.

Identification of a Neolignan Glycoside from the Pine Tree, Pinus densiflora Showed Antithrombotic Activity